


The Adventure Ends in Chaos

by loveyoutoobits (lostflares)



Category: Check Please! (Webcomic)
Genre: Caitlin's POV, Chowder loses an arm but its ok, Fantasy, Gen, I can't tag this in completeness without spoiling the ending so that's all you're getting, Ogres, Pirates, monster of indeterminate breed, no major character death or graphic violence but there is death and violence, sharks (as in the animal)
Language: English
Status: Completed
Published: 2019-06-06
Updated: 2019-06-06
Packaged: 2020-04-11 11:15:15
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 10,295
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19108528
Author URL: https://archiveofourown.org/users/lostflares/pseuds/loveyoutoobits
Summary: Caitlin is the defacto leader of the odd questing group consisting of Caitlin as the ranger, Chowder as the rogue, Dex as the cleric, and Nursey as the bard. They travel from one land to another, across the ocean, fighting an ogre, a group of pirates, and the beast of Riberia, which proves a tough nut to crack, even for the somewhat experienced adventurers.





	The Adventure Ends in Chaos

**Author's Note:**

> There's a major twist at the very end of this fic so I can't give you more in the tags or the summary. 
> 
> Thanks to my beta thelady-mondegreen for baring with me!
> 
> There's wonderful art for this fic created by omgtranspoindexter! Art is here: https://omgtranspoindexter.tumblr.com/post/185395817667/the-adventure-ends-in-chaos-written-by

                                                              

Caitlin looked down through the trees from her position. Their target sat just ahead, feasting on some poor creature. They were of course hired to keep it from eating anything else, but not much they could do for that one now. She kept her bow at the ready, with an arrow nocked but not drawn, ready to pull back at any moment. Glancing down, she gave a subtle nod to Chris, who had been hiding in the bushes at the base of her tree. He nodded back, before slinking through the shadows closer to the beast.

Caitlin watched him move for a moment, before returning her gaze to the target. He wasn’t a big ogre, rather than tall he was fat. Probably that way thanks to the farm animals he had snatched from the local village around the bend. The creature he munched on now looked to be a deer, so not from the village. They had been lucky to corner it in the forest rather than closer to the village, though it was more like they had accidentally stumbled across it and only just managed to remain undetected. Will and Derek had gone off to surround the ogre, while Caitlin and Chris had hung back for surveillance.

In a moment, Chris would sound the signal, and they would all attack. That was the general plan. Whether or not Will and Derek would keep from fighting long enough to cooperate and whether or not Chris would be able to get in close enough was why Caitlin was up a tree, far enough back to not be seen, but close enough to fire a dozen arrows before the ogre could figure out where they came from. Caitlin kind of expected to shoot a dozen arrows. All their previous quests had ended with Will and Derek arguing and Chris with a bump on his head more often than not.

She took a deep breath, and heard the signal from Chris. As planned, Chris charged down the center while Will came in from the left and Derek came in from the right, but that was all that worked from the plan. The ogre wasn’t as distracted with his meal as they had hoped, and Chris couldn’t get close at all, instead getting kicked in the stomach. Will had better luck, but his sword barely made a dent. Caitlin… wasn’t sure what Derek was trying to do, but it did annoy the ogre enough where it turned to him instead.

Caitlin sighed and loosed five arrows into the ogre’s head and it dropped to its knees. Caitlin watched the chaos that was the boys, as Will and Derek argued and Chris huffed, trying to catch his breath. She scrambled down from the tree and the boys had enough sense to stop arguing when she approached.

“Right. So what have we learned from this?”

“I should get a bigger knife.”

“No, Chris.”

“I should really get a better sword, instead of just trying to fix this one.”

“Will.”

“I should write a new poem.”

“Absolutely not.” Caitlin shook her head at the three of them, before taking a piece of the ogre as proof of the kill. She didn’t know why she put up with the three of them, but it wasn’t like she had any other choice.

“Let’s get our money and get out of here, shall we?”

* * *

 

They were on the road from the ogre problem village for a couple days before coming across the next village. They had been planning on leaving the land entirely, heading for the sea and some other land, where new adventures awaited them beyond distant shores. Or at least, that’s how Derek called it. Caitlin called it ‘earning enough to leave the shithole they were in behind’.

This town happened to be the biggest port town in the area, with a sizeable harbor and plenty of ships to pay for passage on. They hadn’t decided on a destination, so Caitlin suggested they get rooms at the inn, to discuss and to have a good meal and a warm bed. The boys, tired, readily agreed.

They entered the Singing Ferry, a cheerful looking inn close to the water’s edge, a small distance from the edge of the dock, out of the way while still being central. The boys took seats at a table in the corner, leaving Caitlin to get the rooms. She got two rooms and ordered four meals, before returning to the boys.

“So, Cait, where do you think we should go?” Chris had spread their map on the table, one finger on where they happened to be. There was a lot of sea from here to anywhere else, and Caitlin looked for anywhere of interest, before shrugging. She didn’t know much of the area other than where they had been, it being all she had known.

“I think we should head west, though I don’t know anything about the area here.” She pointed to a spot on the map, where a large continent sat. All three boys looked at it with mixed reactions. Chris looked thoughtful, Derek almost gleeful, while Will just looked glum.

“I’d rather not go back there if I can help it.” Will tapped his finger on the table, looking at the others with hope in his eyes.

“Oh, but it’s got some of the best musicians of the time! Maybe I can learn some new ways to annoy the monsters.”

“You can do that by existing--”

“Derek. Will. No arguing.” Caitlin had learned enough about the pair to know that they would be at each other’s throats if she didn’t stop them early. Turning back to the map, she tapped at another spot. “What about over here?”

“Oh, I’ve heard of this place! Known for its beaches, its castles, and its monsters that seem to never end! Plenty of opportunity to earn some cash.” Chris looked almost too cheerful considering what he had just said, but she nodded in agreement. What he said sounded good, and the other two didn’t happen to have any complaints.

“Ok, so our next stop is to Riberia.” The other three nodded, and Chris folded the map, just as the innkeeper brought them their meals.

“Riberia? Isn’t that place cursed? A group of adventurers like you might fair well, but be warned of the beast of Riberia. I’ve heard tales that this creature has never been killed, even among the undying monsters that reside there. Many have tried, and none have succeeded.” The innkeeper shook his head, before turning away without another word.

They ate in silence after that, though their plans hadn’t changed at all. They would still head to Riberia. There was almost nowhere else for them to go.

* * *

 

They were just finishing their meal when a man burst into the inn, soaking wet and scowling. Considering it wasn’t raining, Caitlin could only assume he had fallen in the water. The innkeeper stopped his task at the bar, and scowled at the sopping man.

“Hamish, what have you gotten yourself into this time?”

“If I said mutiny it wouldn’t be as bad as what’s occured.” Hamish took his hat from his head, slapping it wetly against his thigh, as if that would get the water off it. He looked rough around the edges, well weathered, and slightly crazy. Caitlin thought that she’d like to stay as far away from him as possible, though she had a feeling that she was out of luck.

The innkeeper stared at the growing puddle at Hamish’s feet, and sighed, gesturing for Hamish to come sit at the bar. Probably deciding there was no keeping the water out of the floorboards. “Come on, let’s get you warmed up; an ale and a meal for a tale.”

“Much appreciated, Bob. I knew I always liked you most of your brothers.”

“You’ve had to deal with me most, so I should hope so.” The innkeeper slid a tall foaming tankard towards Hamish, and Hamish took a big long gulp, before tearing greedily into the food that had been placed in front of him. The innkeeper let him eat for a moment, before finally asking. “So, what happened? Why would mutiny be better?”

“Then at least half my crew would still be alive.”

It was clear the few people in the inn had been eavesdropping, because a hush fell upon the room. Hamish didn’t seem to notice, but Caitlin watched as a couple patrons crossed their chests in silent prayer.

Hamish continued after another gulp of his drink, which the innkeeper refilled as he talked. “You see, it’s been only a week since I left this port, and landfall is a good two-odd weeks west of here. On a good wind, the fourteen days would be all that’s needed, and the island halfway from here to there wouldn’t be used. A bad wind, the fourteen stretches into double. But you know this, Bob. So how is it that I’ve returned in only a week? It takes that long to get to the island.”

He had the entire inn’s attention, and Caitlin was beginning to suspect he knew it. He reminded her of Derek, a flair for the dramatic. He could be a bard if he had the face for it.

“You see, only three days west of here, trouble found us in the Idorian sea. If it was a storm, it wouldn’t be as bad. If it was mutiny, I’d have been let off at the island. No, I tell you now, passage west of here is more cursed than landing in the west. There be pirates in the waters.”

There was a gasp in the crowd, and a few more patrons crossed themselves. Pirates to Caitlin didn’t seem all that bad, but Hamish wasn’t done with his story.

“They ambushed us in the middle of the night, none of us were ready. The damn crow’s nest brat had fallen asleep at his post, no warning to be at the ready, no hope to ready ourselves before we found ourselves boarded. A few brave souls, may they rest, took up arms, but were struck down quickly. A few tried to flee overboard, and I can only assume they found rest. The pirates’ captain stepped aboard my ship, looking at it as if he had already blown it with holes, instead of just waltzed on with barely a fight. There would’ve been a fight too, if there hadn’t been more guns and swords on their side than I had seen in my life

The captain had stepped forward, asking us who our captain was. Luckily, I’m no coward, and I stepped forward as far as they allowed. He had looked me up and down with a sneer, before telling me he would be taking my crew and all my supplies, leaving me the boat. My life and theirs were spared, so I didn’t fight it, but as they shuffled over to their boat with my crew and all my ship’s belongings, he gave one last glance to me, before ordering them to sink me. I don’t think he realized how weighted down my boat had been, with all the bodies and all the supplies, because the ship full of holes didn’t sink, and I still stand before you. She didn’t sink until she was close enough to the port for me to swim the rest of the way. I’m only sad to see her go after all these years.”

The inn was silent. The innkeeper was gaping at Hamish by the end of his story, though Caitlin couldn’t tell from what: surprise, disbelief, pity. Hamish downed his drink, finished his food, and then finally acknowledged the room with an appraising stare. His eyes landed on their table, and Caitlin inwardly groaned.

“You lot. Adventurers?”

“Yup. Your tale was very sad, sorry for all your losses.” Chris responded. Caitlin could kick him, but she knew his disarming attitude was better than his actual disarming ability.

“Where are you heading from here? East into the country or west to the sea?” Hamish for some reason looked hopeful, and Caitlin could only imagine what was going through his head.

“We’re heading to Riberia.”

Hamish gave a low whistle. Then he shook his head. Then he gave them a hard stare. After a long, awkward silence, he finally said something. “I’ll pay you to protect my ship, and I’ll take you to Riberia, free of charge, if you can get us there.”

“What, the ship at the bottom of the harbor?” Derek said. He was the most annoying bard in the world. Caitlin kicked him, but he was used to it.

Hamish glared at him, looked around the group of four, before finally deciding he’d address Caitlin. “No, a different ship. The one that sank, the Helena, she was only one of three in my posession. The Seraphina is out on an eastbound delivery, so all I’m left with is the Medusa. She’s the oldest ship I’ve got, and I rarely take her out. But a captain needs a boat and needs the sea. She’ll sail, and sink, unless you accept the job.”

Caitlin considered the old man. He had dried only slightly in the warmth of the inn, and she thought he still looked crazy, but she could admire the willingness to go back out even after such a tragedy. There was one glaring problem.

“What will you do about a crew? The five of us can’t sail a ship.”

“No, that we can’t. However, there are always able bodied sailors here. Though, none in this inn. They will be drinking a storm in the Salt Grotto at the center of the docks. If you’ll join me, we’ll go recruiting.”

Caitlin looked at the three boys. Chris was already excited, though she knew he might have been looking forward to fighting the pirates. Will was contemplative, though he was tapping his fingers, a sign he was thinking of things to fix. Derek looked the most nervous, though she had no idea why. She sighed. It was free passage to their destination, and it would be a paid journey.

“Alright Hamish, you’ve got yourself a deal. We’ll join your crew for the journey to Riberia, and protect your ship.” Caitlin stood from her seat, and shook hands with the sea captain, who smiled for the first time, a twinkle in his eye.

“Sleep, then, adventurers! For in the morning we recruit us a crew, and overmorrow we sail for Riberia!

* * *

Recruitment started bright and early at noon. Hamish had come knocking on their doors, and rather wide awake, the four of them had asked why it was so late.

“Sailors just returned drink til the morning then sleep til noon. Then they sail off again and repeat the cycle. They rarely get the luxury of that much down time so they take advantage. Now we go to take advantage of the cycle.” And with that, he turned and led them to a ramshackle bar that could barely be called an inn, with a sign half off its pegs with a wind battered and faded Salt Grotto painted half heartedly across it.

The smell inside wasn’t unlike most bars, if you counted sweat among the smells in a bar. Sailors that hadn’t managed to make it to their rooms were still slumped over tables with tipped over tankards beside their hands, and some had chosen the floor as their bed. Hamish appraised them slowly, took a deep breath, and shouted.

“Up and on your feet, men! The sky is clear and the wind is right! Who sails west and needs a boat to crew?”

Heads shot up around the room, some more groggy than others, confused as well as alert. After a short scramble, ten men, a few who had come from the rooms upstairs, stood in front of Hamish. He walked along the line, muttering to himself, before stopping at one end.

“You, sailor! What experience have you in fighting?”

“I’ve used a sword all me life, capt’n.” The sailor said with confidence. Caitlin could see a cutlass strapped to his hip, and she knew Hamish had noticed as well. He nodded, and moved along the line, each sailor with some experience with some type of weapon. He reached the last sailor, who jumped nervously when Hamish stopped.

“And you, have you held a weapon before?”

“N-no sir. I’ve only just arrived in this country, and I just want to sail home.” He stuttered out, looking down the line of sailors and also at Caitlin’s group.

“Where be home for you?”

“Riberia sir.” He paused, panicked, then continued. “But! Although I cannot fight, I can sail, that is something I’ve done for a long time.”

“Well, you’re in luck then, son. We’re heading to Riberia tomorrow, and sailors are what we need.” And with that, he turned to the door. He glanced around the room at the sailors who hadn’t offered their services, and gave one final send off. “If you wish for pay as soon as tomorrow, and you weren’t in this first lot, you will still be welcome... if you arrive at dawn.”

He left the bar, and Caitlin signaled for her group to leave as well. She didn’t look back, though she could hear the mutterings from both the new crew and the sailors. A few times she heard pirates, other times she heard the beast of Riberia, and then the door closed behind her and she only heard the seagulls.

“Alright, recruitment is done! If you don’t mind helping me prep the ship before the morrow, that would be greatly appreciated.” Hamish stared at the group hopefully, and Caitlin glanced around. Chris and Derek shrugged, though Will somehow looked excited, probably due to the carpentry deity he pledges to.

“Sure, what do you need us to do?”

* * *

 

Turns out, what he needs them to do is essentially get the boat into the water. But first, scrubbing it head to toe, fixing broken railings (Will did that), and acquiring cleaner supplies for the crew’s quarters and the galley. Of course, the hardest part with five people was getting the ship in the water, but only Chris ended up slipping, and Derek sang motivational songs, which was annoying. Eventually, the Medusa bobbed in the water, her freshly buffed figurehead twisted in a grotesque scream that stood out in the sunlight.

Hamish stared proudly at his ship, the oldest one he had, the one he never sailed because he had two others, the one he had hired them to protect from pirates. Caitlin was beginning to feel nervous, staring at the pride on Hamish’s face. She wouldn’t necessarily say that her group was incompetent, but she would say that they weren’t the best at their job. A ranger, a rogue, a bard, and a cleric aren’t necessarily the best suited to wage a battle at sea. She only hoped they wouldn’t have to.

Hamish dismissed them for the day and they returned to the Singing Ferry, tired but excited for the journey. They again took their table in the corner for dinner and the innkeeper brought them their meal, lingering a bit, hesitating to say anything.

“You know, Hamish is a good man, with a good heart. He is a great captain, loyal beyond anything, a good friend. I do have to warn you, though, that he’s probably going to be looking for a fight with the pirates, as he’ll want what’s left of his crew back. I hope I’m wrong, but prepare for a fight, and for Hamish to jump in the middle of it.” The innkeeper turned and left, the quartet staring at their plates in silence.

Too late to change their minds now, she thought.

* * *

 

At dawn, they rose and walked to where the Medusa was docked, glancing at each other in mild apprehension. They were well acquainted with quests like these going wrong, though normally by their own fault. Everything that had happened so far had been so tame, they knew something big was bound to happen sometime soon.

Hamish was addressing his new crew, which had grown to a grand total of fifteen. “Alright men. Today we begin our journey to Riberia. We sail into infested waters, where I’ve already lost a crew and a ship. There be pirates, but we’ve got these fine adventurers to aid us in our journey. They have also agreed to help sail and mind the ship, so although they won’t stay in the crew’s quarters, they will be just as you are, in this crew. Aid them as they aid us.”

The sailors glanced at Caitlin’s group, taking longer glances at Caitlin than the others. Hamish noticed the stares, cleared his throat, and spoke again. “This young lass here is a sharper eye than you lot. Any trouble she brings can be dealt with by her own hands.”

It didn’t satisfy the sailors, but they didn’t complain all the same, probably eyeing her bow, maybe assuming she knew how to use it. Hamish gave a few more words to the crew, before the twenty of them all filed their way onto the ship. From this dock, was the sea, and from the sea, was their destination. To Riberia, through pirates and monsters and the like.

* * *

 

It took three days riding the wind west before they saw another sail on the horizon. Hamish stared hungrily at it, his spyglass never leaving his eye. Caitlin sighed. He had definitely been hoping to run into the pirates again, seeking the return of his real crew. She felt bad for the fifteen souls who watched the approaching ship in apprehension.

Caitlin scrambled down from her spot at the crow’s nest, as one of the crew scrambled up to take her place. Chris had found his place helping the sailors with the sails, nimble on feet, scrambling up the rigging without issue. Will was content to patch the holes that sprung up in the old ship, his hammer seeing more use in three days than his sword had seen in three weeks. Derek chose to annoy everyone on the ship with sea shanties he had heard from a people who had never seen the sea. Well, it annoyed Caitlin, the sailors seemed to like it well enough.

Caitlin wandered over to talk to Hamish, who still hadn’t taken his eye off the ship. She wondered if he could see something there, or maybe he was just crazy, imagining the ship flying the jolly roger. He lowered the spyglass at her approach, the wild gleam in his eye fading as he focused on her.

“Well, lass, what do you think? A fight on our hands?”

“The ship is still too far away to say for sure.” She paused, but it was time to voice the concern. “Did you really hire us only to protect the ship, or did you really want your crew back, with our help in the fight?”

Hamish appraised her for a moment, before he shrugged. “The ship would need protecting either way, I figured, two birds, one stone, a healthy group of adventurers to ferry and fight beside.”

Caitlin had to admit that the captain was growing on her, though she still wasn’t happy about being tricked. Even if she had seen it coming. She really hated that she had missed all the signs, even if she had known something was wrong. Hamish brought his spyglass back up, pointing again to the ship. His grin didn’t inspire any confidence in Caitlin.

“If my eyes are blind, I’d still see the black of that there flag.” He passed her the spyglass, and she took it, pointing it at the swiftly approaching ship, groaning as she saw he was right: snapping in the wind was a black flag, standing out from the blue of the sky and the white of the sails.

“Right then, look lively crew, because if we’ve spotted them, they’ve spotted us, and no amount of gorgons will keep them from our path if they smell profit.” Hamish clapped his hands together, and Caitlin returned the spyglass. Most of the crew looked worried by the prospect of a battle, and the Riberian native peeked out from the crow’s nest with a face creased with worry.

Chris stopped scaling the rigging, swinging like a monkey to stand next to Caitlin in the front of the ship, while Will came up from below and Derek stopped singing. The four of them knew what was at stake in this battle, and there was no going back. Caitlin hoped their track record wouldn’t actually make this battle a losing one. She was still hoping to land in Riberia in one piece.

Of course, the ship was still a ways off, so Hamish was only causing undue panic amongst his crew, and all they could do was wait. It took another hour or so of sailing with the wind before the ship was clearly aiming for them. Its guns were leveled at their bow, and Caitlin figured they wouldn’t try to board them or anything, instead sending them to the bottom of the sea before asking any questions. Too late now.

“Hamish, are you sure you know what your doing? You might’ve just gotten lucky the first time.” Caitlin spoke to the captain quietly so that the crew wouldn’t overhear them.

“Pah, what’s luck got to do with being ambushed by pirates? They sunk that ship and they’ll sink this one if we don’t fight back! They’ve got their guns and we’ve got ours!” Hamish was decidedly less quiet, and the crew began to mutter amongst themselves. Well. At least Caitlin tried. It was too late to outrun the pirates now anyways.

The first shot of cannonballs missed, falling just short of the bow of the ship, but it was still too close for comfort. The next round wouldn’t miss. Hamish began shouting orders for the crew to man the small smattering of guns on the ship, firepower against firepower. Caitlin knew that their ship only had about 10 guns, and from what she could see, the pirate ship had about twice that just on its upper deck. So, they were sunk.

The pirate ship was close enough where they could hear the faint order to fire, and Caitlin braced herself on the railing, waiting for impact. She noticed that the pirate ship wasn’t firing all their guns yet, so instead of 50 cannonballs, only 15 came flying their way, most of them missing, but one hitting the part of the bow just beside the figurine of Medusa. Hamish gave his own return call for fire, but all ten shots fell flat, missing the pirate ship completely.

As they waited for the pirate ship to come somewhat closer, Chris and Will went to help with the guns on the deck and Derek did… whatever he usually did. Caitlin did notice that some of the crew relaxed somewhat as Derek played, and they didn’t rush as much as they tried to load the guns, so she shrugged it off. She stayed by Hamish, not needing to be up at the crow’s nest or needing to draw her bow just yet. She had a trick up her sleeve that she was hoping to not have to use, but for now she was among the sitting ducks that resided on the Medusa.

Finally, the pirate ship came within range for the Medusa to be boarded or destroyed. They had been firing every so often, breaking holes in the ship that left Will scrambling to keep things together, though none of the holes had been catastrophic yet. The pirate ship towered just slightly above their ship and Caitlin didn’t have a good angle to go cherry picking with her bow, so she stood her ground, holding her breath.

The first grappling hook sunk its teeth into the railing on the ship. It was followed by a half dozen others. Hamish called for the lines to be cut, but as soon as one rope was cut it seemed like two others took its place. Caitlin finally had targets, and she went cherry picking as the pirates crossed the lines to board the ship. Of course, she didn’t always hit them, but she did get a few, who dropped heavy into the waves between the two ships.

The battle started right away, with Hamish’s new crew rushing around in a frenzy, trying to keep their heads in more ways than one. One of the new crew already lay ominously still on the deck, but Caitlin didn’t have time to focus on that. She ran out of arrows at the ready, instead pulling her dagger. She looked around for the rest of her group, spotting Will cutting down pirates with little issue, Chris was sneaking around back stabbing those that failed to notice him, scurrying away from those that did. And Derek was… being Derek. His lute was in hand and he was alternating between singing a calming song and shouting insults at the pirates. At one point he got frustrated by whatever and swung his lute at a pirate’s head, miraculously not breaking it in the process.

Caitlin was satisfied that the boys could handle themselves, so she threw herself into the fray. She decided to go Chris’s route more than Will’s, backstabbing when she could, dancing around the ship, picking up any arrows she came across, replacing them in her quiver. She got to the ropes, seeing that there were still pirates on their ship, either lined up to make sure none of Hamish’s crew made it to their ship, or waiting for more room to be made on the considerably smaller Medusa’s deck. The chances for both were high, but she figured it would serve them more to cut the ropes as often as they appeared.

Her dagger was sharp, but not sharp enough to cut through the thick ropes in one motion. It took almost a minute to cut the first rope, and Caitlin had to keep glancing behind her to make sure she wasn’t in any danger. This caution divided her attention to the point that she missed something glaringly obvious. So focused on the left and the right and in front of her, she didn’t check being her until it was too late, and she toppled over the edge of the railing down towards the sea.

* * *

 

Caitlin could swim. She had always prided herself on her ability to swim. It wasn’t helping her at all after having been plunged several feet deeper than her lungs depleted of air could handle. Her thoughts were muddled, but begging for help from anyone who would listen was something she could do in any situation.

She kept trying to kick her way to the surface, weighed down by her clothes, unwilling to part with any of her gear. She had worked hard for all that she owned, and she’d rather give up her life than her earnings. Or at least, that was the thought through her head as she drowned. She felt something hit her feet, than another hit her hand, but she continued to look up, at the shifting light and the underside of two boats.

It took her a second to realize she had latched onto something with her free hand, and that she was moving considerably faster than before. It was just as well, because her legs had lost a lot of strength. Another few seconds later, and she breached the surface, gasping for air, holding onto dear life to whatever it was that had saved her. After her throat had caught up to her, she looked around, and down at her hand. She gasped at what she saw. In her hand was a dorsal fin, which in turn was attached to a reef shark about as long as she was tall.

Caitlin wasn’t afraid of sharks. She knew better than to be scared of them. They only attack when provoked or confused. However, she had never heard of sharks, let alone more than one, helping someone. Including the one she hung onto, there were three others swimming around her. Well, she had asked for help.

She looked down at the shark she held onto, then up at the two ships. She could hear the distant clang of sword against sword from the deck of the Medusa, with shouting mingled in. She thought she heard her name a bit, but she was really too far away to hear anything distinctly. Looking back to the sharks, they seemed to be waiting for something. She hoped maybe for some orders from her.

“Um, can you get me up to that ship?” She pointed at the Medusa, but she figured it was hopeless, and the shark practically shook its head in reply. “Alright then. New plan. If I can’t get up to the ship easily, we’ll just have to help from down here.”

She shrugged her shoulders, and then straddled her shark like it was a horse, pulling a rope from her pack. It was hard to tie the wet rope, but eventually she had a sort of seatbelt keeping her attached to the shark’s back. The other three sharks looked at her expectantly.

“Ok then. We’re going to attack the pirate ship from here. The three of you, go for the keel. I’ll go cherry picking.” Caitlin pulled out her bow, glad she hadn’t unstrung it. She had significantly less arrows than she would have liked, but they would have to do.

The three sharks swam beneath the surface, hopefully to do her bidding, and the shark she was on swam a good distance away from the Medusa where Caitlin could see the deck and the people on it, and still take the shot. She saw Chris fighting a couple pirates at the railing. He looked angry, and he wasn’t trying to run away. He wasn’t the best at close combat, so Caitlin did what she could do. She aimed at the closer pirate, and willed the shot to go straight. Of course, she couldn’t really do anything except let the arrow fly.

It flew into the back of the pirate, and Chris, although shocked, managed to dispatch the remaining pirate, before looking over the edge in Caitlin’s direction. His anger seemed to melt away, and a wide smile spread across his face. She waved at him, and he gave a tiny salute, imperceptible to anyone but the two of them. He turned away from the railing, running out of sight. Caitlin breathed a sigh of relief to know at least one of them was alive.

It took some time, but she ran out of arrows, most of them finding the targets she had aimed for. She slung her bow back on her back, unsure of what to do next. She heard from behind her a horrible creaking noise. When she looked back at the pirate ship, one of the sharks she had sent to the keel came up with a chunk of wood in its teeth, which it showed her before dropping. Caitlin could now hear shouting from the deck of the pirate ship, though she was too close to see the deck. Directing her shark to the side of the Medusa, she watched as someone shouted orders, and some of the pirates seemed to disappear below decks.

One pirate came running up from below, soaked head to toe, and Caitlin figured out what the sharks had done. They had ripped a hole in the bottom of the ship. It would sink long before any of the holes in the Medusa would sink it. Satisfied with her contribution, even if it was slow moving, she untied the rope holding her to the shark, and grabbed onto a rung of the built in ladder. The four sharks watched as she climbed part way up the side of the Medusa. She felt a little silly, but she had been saved.

“Thanks for all your help. You can go home now.” The sharks seemed to nod at her, before sinking below the waves again, disappearing completely from her view. She shrugged her shoulders, and began to climb.

* * *

 

She reached the deck after a few minutes, a bit out of breath from her non stop exercisions. She poked her head up and looked around the deck, trying to stay out of sight while trying to figure out what was the state of things. Everyone on the deck was still fighting. She saw both pirates and sailors alike lying motionless on the deck, but there were fewer sailors. Maybe because there were fewer sailors to begin with. She spotted Chris, who had gone back to backstabbing, and a pang of relief swept through her. A moment later she heard, rather than saw, Derek, as he shouted insults and played his lute. She scanned the deck for Will, finally spotting him by his hair on the far side.

She pulled herself up carefully over the side of the railing onto the deck, taking care not to be spotted. She was almost successful, but Hamish noticed her, and figured he’d draw attention to her.

“Oi lass, did you do that?” He shouted across the deck at her, drawing the attention of several battles, but luckily people were too busy trying to kill and not be killed to try and knock her off the boat again. Caitlin wound her way through the crowd towards Hamish, who finished dispatching his opponent.

“I had some help.” She left it at that. It would’ve been crazy to explain about the sharks.

“Well, whatever you did, it took the wind out of their sails. When that noise from below came up, it even tore into my heart, and I wanted to sink that ship from the moment I saw her.” Hamish watched the pirate ship as it slowly sank.

Caitlin took a second to watch the fights going around, and realized that the pirates didn’t seem into it anymore. They had stopped being on the offensive, mostly fighting back to stay alive. They had noticed the state of their ship. It was either stay and fight to the death or go down with their ship.

It only took a few more minutes before the two decks, previously at different heights, were lined up. Pirates on their deck stared in disbelief at the Medusa’s deck, but they didn’t make any move to come over. The ropes had been cut. Hamish nodded in satisfaction, but then did something that caught Caitlin off guard. He whistled a long, loud whistle, and the fighting slowly petered off, sailors and pirates staring at the old sea captain.

“Listen up, you scumbags! I am a lenient man. It doesn’t bring me joy to see a ship sink with her crew aboard, regardless of who that crew may be. If you will not kill me and my crew, I’ll let you aboard my ship, and I’ll let you live. As long as you abandon your piracy.” Hamish seemed so sure that it would work. He seemed to stare down everyone on that ship and his own all at once.

The pirates on their ship were the first to move. They approached the edge of their railing, staring at the distance between the two ships. There wasn’t a way across. Then one shrugged, and cut a rigging rope, taking a running leap, before swinging across the gap, dropping down onto the deck of the Medusa, tumbling forward until he was back on his feet, before turning to face his sinking ship. With a nod, a few others took his cue, and, as the rope swung back to the pirate ship’s deck, pirate after pirate swung across the gap, until only a few remained.

“I can’t believe that worked.” Caitlin gave Hamish an appreciative glance, but Hamish was beaming with pride.

“Well, half of them were from my old crew, so I knew they wouldn’t go back to being pirates if they lived.” Hamish moved from where he stood, going through the groups of people had stopped fighting. Caitlin looked around for the pirate captain, but she assumed he had elected to go down with his ship, just like Hamish would.

Caitlin’s group finally managed to come back together, everyone a little worse for the wear from when they first got aboard the Medusa. Chris had fresh cuts on his arm and his chin, and there was the sign of a bruise blossoming on his chest. Will had scrapes along his forehead and a few new chinks to his armor, and Derek’s lute was missing a few strings and he was sporting a black eye already, and had a cut along his arm. Caitlin, for her part, was still waterlogged, and probably had a bump on her forehead from when she hit the water. They certainly looked like a ragged group of adventurers. But at least they were alive.

“Come on, we should go help Hamish with cleaning up.” Caitlin said. “We can rest when they do.”

“I know we needed to get on a boat to get to Riberia, but did we have to get on this one?” Chris asked, rubbing at the bruise on his cheek. Will nodded, but Derek grinned.

“I for one found it exciting! The type of story a bard loves to tell. A heroic battle fought at sea, where the opposing ship sank and half the crew chose life over loyalty! What could be better for an epic?”

“I don’t think that’s a very epic story. Not if you’ve lived it.” Will responded. Before the two of them could start bickering, Caitlin shoved them in the direction of Hamish, who was addressing the new crew of the Medusa.

* * *

 

After the first battle on the Medusa, the ship was smooth sailing until the restock island. They were only ashore for a day, picking up new supplies for the much larger crew, staying the night before leaving in the morning.

The following week passed without incident, and the final leg of their journey to the coast of Riberia ended with only the normal wear and tear one expects on a boat. They docked at the port town that was eerily similar to the one they had left two weeks prior, and watched as the crew disembarked for the local tavern somewhere along the harbor.

Caitlin’s group stayed behind with Hamish after he had asked them to. She hoped that this would be when he paid them, but she was getting the sinking suspicion that Hamish didn’t actually have any money to do so. She was pleasantly surprised when he handed her a bulging coin purse.

“Here lass, you did exactly what I had asked of you lot, even if I had lied about my intentions at the beginning. So, your passage was paid for by your work, and your work was paid for by this.” Hamish tapped the bag in her hand. “Welcome to Riberia, enjoy your stay, and try not to get eaten by the beast.”

Hamish left his ship, following the direction his crew had gone. Caitlin was almost tempted to follow, but she was about ready to be done with everything to do with Hamish, so instead, she pointed in the opposite direction, hoping for an inn.

“Let’s get a room for the night, figure out what to do next. I don’t want to look at a boat for at least a day.”

The boys nodded in agreement, and the four wobbled down the gangplank, trying to get their land legs back. Leaving the bustle of the harbor behind, they looked around for an inn and a supply shop, two things they’d need before embarking on a new journey.

They also just so happened to be in the same location in the middle of town. The group pushed their way into the Bear’s Bane, to be greeted with a familiar tavern level of the inn. The boys grabbed the table in the corner, and Caitlin ordered the meals and the rooms, before going to sit in the corner. It’s the same sense of deja vu no matter where they go. Like every quest they go on is just the same one in different locations.

Sure enough, someone bursts into the inn, angry and irate. This time, though, it’s a woman. She goes straight to the bartender, who passes her a ready made tankard with no questions asked. She downs it quickly, before gesturing for more. It takes her three full tankards before she seems a little calmer.

“Ben, someone has to do something about that _beast_!” She says it with such disdain, Caitlin wasn’t entirely sure she was talking about the beast of Riberia.

“Amara, you know it’s damn near impossible. The best someone’s done in these last few years is take an eye out, and that only made it stronger.” Ben the bartender cleared up the confusion.

“Yes, but there has to be someone strong enough! That beast has destroyed the lives of us all!”

“Who died?” Ben had no tact, but this was how stories progressed.

“Devan. He was only out in the Greater Woods, but the beast keeps creeping closer and closer to us. It’s only a matter of time before it reaches us here.” Amara took a gulp from her fourth tankard full.

“There’s nothing we can do on our own. A group of adventurers might be able to take it down, if they have the right strength.”

And with that, Caitlin hoped to god this wasn’t their quest. What can a ranger, a rogue, a cleric, and a bard do against a beast? None of them had any real fighting skills. There’s nothing they can do against a beast that powerful. Regardless, Caitlin kept an eye on the pair as they continued their conversation loudly in the relatively empty tavern. It slowly diverged from the topic of the beast, and Caitlin breathed a sigh of relief. They can’t take the beast just yet. No way.

Then all hopes were dashed when Amara scanned the room, with her eyes landing on the four of them. Caitlin groaned, and the boys quickly glanced in the direction of her attention, before they all sighed. At least they knew there was some trouble afoot. Amara had gotten up and slowly made her way to them, just a tad past drunk. Maybe a quest offered by a drunk doesn’t count.

“You lot. Are you adventurers?” Amara’s words were slurred, and her pointing wavered in the space around them.

“Well yes, but--” Caitlin tried, she really did. But there’s only so much you can say before a drunk offers you a quest.

“Go slay the beast of Riberia. I’ll pay your weight in gold.” Amara should not be offering a sum like that in her state.

“Do you even have that kind of money?” Will asked, and Caitlin was glad he was always such a skeptic.

“No. But the beast does, from years of killing. You can have all its wealth when you take it down. We won’t ask for a penny of it.” Amara wasn’t one to be swayed, apparently.

“We have just arrived in town. Can we have some time to accept or not? Like, the morning, maybe?” Chris was too nice for his own good sometimes, but he really did have the type of attitude that made people want to make him happy. Amara didn’t seem any different. She paused, before nodding.

“I’ll be back at the same time tomorrow, and I expect an answer!” She swayed on her feet. She probably wouldn’t be awake until this time tomorrow. She left without another word, leaving the four of them to contemplate an impossible choice.

* * *

 

They went up to their rooms, arguing the whole way. Caitlin and Will were against the battle, knowing it was more than likely going to get them all killed. Derek was all for the battle, insisting they’d be rich and treated like kings. Chris was resigned to their fate. One way or another, they’d fight the beast of Riberia. And probably die trying.

In the morning, they trooped down to breakfast, hoping that maybe Amara was too drunk to remember the promise. At least, all of them but Derek felt that way. Derek was raring to go, strumming little motivational songs on his lute, being a general nuisance, insisting they go on the quest, talking about all the new things he had learned to do since fighting pirates.

Caitlin for the most part ignored him. He loved to be annoying, and it was too early in the morning for her to pay attention to anything he said. They sat at their table, the innkeeper brought the meal, and they ate in silence. Caitlin watched the door like a hawk, hoping Amara wouldn’t come in and they’d be able to leave town without accepting a fatal quest.

They were about to finish eating, and about to be able to leave scott free, when the door to the tavern opened, and in walked a very haggard Amara. She scanned the tavern, before picking their table. She stalked towards them like an animal on the hunt for unsuspecting prey. Which means, regardless of their answer, Chris was probably right to assume they’d go on the quest anyways.

“Well, have you decided, adventurers?” Amara’s eyes glinted hungrily, as she closed in for the kill.

“I’m sorry, but I just don’t think we have the right personnel--”

“So you’ll do it? Right? You’ll make sure none of the rest of us die?” Amara wasn’t listening, and she striked, taking them all down.

“Of course! We’ll do our best against this beast of yours!” Derek took the initiative, the only one actually excited to face certain death.

Caitlin’s mind was working overtime. Maybe they can accept the quest, then never actually do it. They’ll never go to this port town again, they can avoid facing the beast at all, leave Riberia from a different port once they’ve done all they wanted in Riberia. The beast will continue to ravage the villagers, but the four of them will live. It’s the only scenario that comes with them living, pretty much.

“Oh wonderful! I’ll have my son take you to the Greater Woods where the beast was last seen. My son’s training to be a doctor, you see, and he needs real experience with injuries, so he’s going with you! Don’t let him die, now!” Amara’s hunting aura transformed into sunshine and happiness and Caitlin went from thinking they can get through this to knowing all four of them and Amara’s son were going to die.

Amara bustled out of there after having successfully captured her prey, leaving three of them glowering at the fourth. Derek looked happy and oblivious to their annoyance. He finally clued in, shrugging his shoulders.

“What? I’ve got a plan! Don’t worry, we’ll win this!” He grinned widely. He had gotten his way, and Caitlin was afraid to find out how their bard was going to fix this mess they’ve found themselves in.

* * *

 

Amara’s son was young, and he introduced himself as Dr. Adam. He was very excited to tag on the doctor title, that, if Caitlin had learned anything from movies, she was sure he was going to die right away. Amara had insisted they leave as soon as possible, and he met them just after they finished breakfast. He led the way out of town, chatting the whole time about how he would make sure they wouldn’t die, how he would treat their wounds so well, how they were sure to win because they were big strong adventurers.

Caitlin didn’t have the heart to tell him that a ranger, a rogue, a cleric, and a bard probably stood just as much of a chance against the beast as all the villagers combined.

“So, he was last seen in this area, where he killed old man Devan. My ma said that the beast sleeps in late, so you’ll probably have to search a bit to find the guy. Can you do that?” Adam bounced on his feet. He probably never got to see any real adventure, this might even be his first time out of the village. Caitlin felt even sorrier for the poor thing.

She was the one with the tracking ability, so, even though she didn’t want to, they were already there, and she went tracking. The beast had large feet, which just made Caitlin even more worried about their fates, but Derek behind her hummed quietly to himself, as if he had the whole thing figured out.

It took another hour before they saw fresh signs of the beast. It had woken up sometime during that stretch, and was moving faster than Caitlin expected. She saw a fresh sign of the beast, some iridescent fur pulled out by a stubborn tree branch, and she held up a hand for the rest of them to hang back while she moved forward. A few more feet, and there was a large clearing with the beast inside.

It was actually kind of beautiful, in a grotesque way. Its fur was iridescent, purple and green, and it was large. Larger than a bear, by any means. It turned its head slightly, and its face was horrifying. It had at least 6 eyes, and razor sharp teeth that couldn’t stay contained within its mouth. It had large drooping ears, and a small flat nose. It’s tail was long like a dog’s, but it twitched like a cat’s.

Caitlin slunk back to the rest of the group. They were in for a real struggle, and they would probably still all die. Derek still looked excited.

“Alright, Derek. Tell us your plan. It better not be stupid and get us all killed.”

“Yo chill. Just attack the thing while I get prepared. This will make us all live, I promise.” Derek tossed up a couple of finger guns that did not make Caitlin feel any better, before he gestured for her to lead the way.

“Fine. We’ll go with a sneak attack plan so that Chris can actually do some damage. Everyone, spread out, don’t get in the beast’s line of sight. It might be hard, since it’s got six eyes. Also, big ears, so don’t make any loud noises. It’s nose is small, so smell shouldn’t be an issue.” Caitlin hoped that Derek actually had a plan. The other three nodded, and Adam looked so excited. Caitlin really really hoped the Derek had a plan.

She led the way back to the clearing, where the beast still sat, like a giant, green and purple, iridescent, six eyed cat. Its back was to them, which was good luck. Caitlin nodded for Chris to move forward, and he snuck up on the beast, before plunging his dagger into it’s back, as high as he could reach. The beast reared up and roared, and Chris hung on for dear life as the beast swung around, trying to figure out where the fly bit him. Caitlin wasn’t sure if Chris did any damage or if it just made it angry, but the battle had begun.

“Adam, stay here. The rest of us, let’s go save our rogue.” Caitlin drew her bow and fired an arrow at the beast’s head, managing to get one of the eyeballs. The beast blinded briefly, Will went on the attack, swinging his sword at the stomach of the beast, leaving a deep gash in it’s underbelly. So far, the battle was actually going in their favor for once.

Derek hadn’t moved from his spot near Adam, his lute still slung on his back. Caitlin barely had time to figure out just what he was planning, but she was angry that he wasn’t helping in the moment. She fired another couple arrows at its head. Chris had managed to pull his dagger free, and he had joined Will in slashing at the beast. All they seemed to be doing is adding injuries and anger rather than damage, but hopefully whatever they were doing was enough.

Caitlin stole another glance at Derek and Adam. Adam looked starstruck, watching the battle progress, but Derek was slowly grinning. Caitlin didn’t exactly like the look on his face, but maybe he was finally ready to join the battle.

She heard a cry of pain that drew her attention back. She quickly turned her head, only to catch Chris clutching at his arm. Or where his arm should be. She looked up at the beast, and watched in horror as the beast chewed on the rest of Chris’s arm. There was no time to wait for Derek to finish his preparations. Whatever he was going to do, had to happen now.

“Derek, get off your ass and do whatever you’re going to do to fix this mess before we all die!” Caitlin threw caution to the wind. The beast already knew they were here, there wasn’t much hope of escaping its detection anymore.

Derek looked at the beast appraisingly, giving it a once over, before nodding, his face splitting into a wide smile. “Thanks for hurting it a whole bunch. I’ve got a trick up my sleeve, it’ll blow your socks off.”

He stepped towards the beast, and Caitlin could only watch. She had no idea what he was about to do, and Will had to move from attacking the beast to protecting Chris from being eaten alive now that the beast had gotten a taste of him. There was only so much healing he could do while his attention was divided, and he couldn’t regrow an arm.

Derek finally stood close enough for whatever he was about to do. He didn’t draw his lute or pull any hidden dagger or anything. He just stood there. He took a deep breath, but paused, looking down at Chris.

“Hey get him out of here, I’m not entirely sure if this won’t get you both too.” Derek gestured with his head at Will, who glared back for a moment, before he had to fend off the beast’s head again.

“You are insufferable. If I could get him out of here I would. I’m a bit busy keeping him alive though.” Will shouted back towards Derek.

“Just do it. I’m probably gonna die anyways.” Chris groaned out. Will had gotten the bleeding to stop, but nothing could be done about the pain on short notice.

“Alright, well it’ll be your funeral if it does you in too.” Derek shrugged, before taking his deep breath again. In a commanding voice, with charisma only a bard had, Derek spoke a single word: “Die.”

The beast stiffened, and fell over. No one moved. Derek had a shit eating grin on his face, and the silence that had fallen over the group extended, until---

“Damn it Nursey! That’s not even something you should know!” Will shouted finally. He slammed his fist on the table.

“You couldn’t have done that before my arm got bitten off? How can I be a rogue with only one arm!” Chris threw up his hands.

“Isn’t that a level 9 spell?” Caitlin asked. She was looking through the handbook, trying to find anything about bards.

“Are you sure? I was keeping an eye on spells I could learn and power word: kill was one of them.” Derek grabbed the handbook from her hands, also flipping through, before coming up to a list of spells. “Oh damn, it does say level 9. My bad.”

“This is why we hate playing Dungeons and Dragons with you, Nursey.” Will tossed his die back onto the table. He had been doing well in the beast battle before Derek pulled his stunt.

“What, because I saved the day?”

“No, because you only read half the rules and follow the ones you want, and then you pull a stunt that makes us have to start a pivotal battle all over again because you did something _you can’t do_.”

Caitlin sighed. They were starting their bickering again. Every time they decide to play a session of D&D they do this. Mostly because Derek always does something like this. He had done it three times already. This session was the longest he had gone before messing everything up.

“You know, Derek, we didn’t have to fight the beast yet. We had the opportunity to stay away for a long while before returning to kill the beast. Us leaving the village in the morning and not accepting the quest would’ve let us live long enough to get strong enough to actually let you learn the damn power word.” Caitlin sighed.

“Oh. Then my bad. But yo chill about this all. We’ll just try again.” Derek shrugged.

“Not today. I’m burned out from this. All that effort to create an interesting battle down the drain.” Caitlin shook her head. Getting up, she cleaned up her things.

“Oh wait Cait. I’ll walk out with you.” Chris cleared up his things too, linking arms with her, and walking her to the door.

“I’m going to my room. I can’t believe you did this. Again.” Will pushed away from the table, leaving Derek alone.

“Hey, wait guys. Where are you going? We can just start over, no harm done!” Derek stayed at the table. “I’ll read the handbook carefully this time! I swear! Hey! Guys?”

But Will was already gone, and Chris had opened the door for the two of them.

“Maybe another time Nursey. Session’s done for the day.” Chris closed the door, leaving Nursey alone with the rule book.

**Author's Note:**

> Thanks for reading my fic! It's a bit different to the things I usually write, so I hoped you liked it all the same!
> 
> Partial disclaimer that I know nothing about DnD as I do not play it and all online stuff is so long oh man. I did plenty of research but it was still hard. I did have a lot of fun writing it!


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